Pioneer Days: An Annual Celebration of Englewood History

The Englewood Pioneer Days Committee has been busy working on the schedule for the 62nd year of this community celebration. This year’s theme, “A Journey in Time,” is sure to allow everyone’s creativity to flow. All current information, contest forms, parade and vendor applications, etc. are available on the web site. Be sure to check back frequently as it’s updated almost daily.

The celebration kicks off with the traditional Little Miss/Mr. Englewood Pageant on Sat. August 18 at the Lemon Bay High School Auditorium, 2300 Placida Rd. There is a small fee to enter or bring a canned good for free entry as it will be donated to the Jubilee Center.

On Sun. August 19, Englewood Bowl, 299 S. Indiana Ave., will host the Community Charity Bowl. The charge is $4 per game (plus shoes) and 50% will go to the participant’s charity of choice. This event runs from 2-6 pm and will be fun for the whole family!

The Kid’s Shipwreck Dance for ages 8-12 is to be held at SKY Academy, 881 S. River Rd., on Fri. August 24 from 6-9pm. This event is free! A DJ will provide music; beverages and pizza will also be available at no charge. Thank you to the Englewood Community Coalition and SKY Family Academy for sponsoring and hosting the dance.

On Sat. August 25, Chalkfest 7.0 takes place at its new location - the Englewood Rec Center (101 Orange Street). Registration begins at 8am. There will be live music and other fun arts & crafts. This is event is free for everyone!

The Teen Shipwreck Dance for ages 13-17 is to be held at SKY Academy, 881 S. River Rd., on Sat. August 25 from 6-9pm. This is another free event! A DJ provides music; beverages and pizza will also be available at no charge. Thank you to the Englewood Community Coalition and SKY Family Academy for sponsoring and hosting this dance. Everyone - for both dances - is encouraged to wear their best 80s getup for a chance at prizes and more!

The Historical Tours will take place on Sun. August 26 from noon to 4 pm. Maps can be found online for those wishing to see parts of Englewood’s history. Thank you to the Lemon Bay Woman’s Club for helping to plan this event and add several more locations this year. 

On Sat. September 1, the Cardboard Boat Race will begin at 9am. Due to Red Tide, the Englewood Pioneer Days Committee and US Coast Guard Auxiliary Flotilla 87 has decided to move this event to the Ann Dever Pool Park on San Casa. This event will allow even the most novice of novices to try to paddle their way to victory. Children 10 & under will be FREE, thanks to Tiffany Square Bingo. Applications are on-line at www.englewoodpioneerdays.com.

On Saturday night (September 1) the Shipwreck Dance returns to Pioneer Park, 300 block W. Dearborn! There will be live music, a beer garden, food trucks and more at this free, family-friendly event. The Englewood Drum Circle will open for Kettle of Fish. So join the fun from 5-11 pm. 

The Lemon Bay Woman’s Club, 51 N. Maple St., presents the Diaper Derby on Sun. September 2 at 2pm. For crawling babies only, sign up ahead of time as the number of entries is limited. The Lemon Bay Woman’s Club is celebrating its centennial anniversary, so be prepared for the appointment of the ‘Centennial Baby’ at this year’s derby. 

That Sun. September 2, visitors can also attend day one of the Pioneer Day’s Festival at Pioneer Park on W. Dearborn St., from noon-8 pm. There will be live music, vendors, a free kids’ zone, and much, much more. The Open Car Show takes place from 3-7pm on Dearborn St. For more information, please visit the website.

On Labor Day (September 2), the Festival Park will open at 8am and the Parade starts at 9am (rain or shine.) A day of entertainment and fun will be going on in Pioneer Park, next to Mango Bistro. There will be contests, more live music, and award presentations. Also, the Corvette Car Show takes place on Dearborn St. from 11am - 3pm. The park will close at 3pm.

This is a celebration of Englewood’s past, present and future. Each year, thousands of visitors gather to share in the celebration of this amazing town. The Englewood Pioneer Day’s Facebook page and website www.englewoodpioneerdays.com has pictures from past events.